NP-MRD: Showing NP-Card for 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol (NP0277249)

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Record Information

Version

2.0

Created at

2022-09-09 01:48:43 UTC

Updated at

2022-09-09 01:48:43 UTC

NP-MRD ID

NP0277249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol

Description

SCHEMBL41500 belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol is found in Citrus aurantium, Eucalyptus delegatensis, Helianthus annuus, Liquidambar styraciflua, Origanum dictamnus, Origanum vulgare and Thymus saturejoides. Based on a literature review very few articles have been published on SCHEMBL41500.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092203482D          

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M  END
> <DATABASE_ID>
NP0277249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC(CC1C1(CC3CC(=C1C)C3(C)C)C1C(O)C3CC(=C1C)C3(C)C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O/c1-15-20-10-18(27(20,4)5)11-22(15)30(14-19-12-23(17(30)3)28(19,6)7)25-16(2)21-13-24(26(25)31)29(21,8)9/h18-19,22,24-26,31H,10-14H2,1-9H3

> <INCHI_KEY>
XWWZJGOBESJRBC-UHFFFAOYSA-N

> <FORMULA>
C30H44O

> <MOLECULAR_WEIGHT>
420.681

> <EXACT_MASS>
420.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.35348232199289

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol

> <JCHEM_LOGP>
5.498577741666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.13359800490606932

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.99509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.864  -3.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.412  -2.867   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.759  -3.868   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.702  -2.945   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.492  -1.841   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.322  -0.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.130  -1.353   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.300  -0.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.111   0.627   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.364   2.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.807   2.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.825   3.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.803   2.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.520   1.065   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.331   0.086   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.428  -0.994   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.267   2.584   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.776   2.890   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.857   4.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.083  -1.679   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.623  -1.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.766  -0.454   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.598   1.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.058   0.989   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.671   2.401   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.380  -0.323   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.733   0.413   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.747  -1.033   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.211  -3.355   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.714  -3.690   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.774  -4.788   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   20   24                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15                                                            
CONECT   17   14   12   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23    8   25                                                  
CONECT   25   24                                                            
CONECT   26   23   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    5    3   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O

Average Mass

420.6810 Da

Monoisotopic Mass

420.33922 Da

IUPAC Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol

Traditional Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol

CAS Registry Number

Not Available

SMILES

CC1=C2CC(CC1C1(CC3CC(=C1C)C3(C)C)C1C(O)C3CC(=C1C)C3(C)C)C2(C)C

InChI Identifier

InChI=1S/C30H44O/c1-15-20-10-18(27(20,4)5)11-22(15)30(14-19-12-23(17(30)3)28(19,6)7)25-16(2)21-13-24(26(25)31)29(21,8)9/h18-19,22,24-26,31H,10-14H2,1-9H3

InChI Key

XWWZJGOBESJRBC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantium	LOTUS Database	35616633
Eucalyptus delegatensis	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Liquidambar styraciflua	LOTUS Database	35616633
Origanum dictamnus	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Thymus satureioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.5	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131 m³·mol⁻¹	ChemAxon
Polarizability	51.35 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28293861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56924154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol (NP0277249)

MOL for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

3D MOL for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

3D SDF for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

3D-SDF for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

PDB for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

3D PDB for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

SMILES for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

INCHI for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

Structure for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)

3D Structure for NP0277249 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-ol)